Stereoselective total syntheses of (-)-(4S,5R)- and (+)-(4R,5S)-chuangxinmycins 1 were achieved based on the enzymatic syntheses of (2R,3S)- and (2S,3R)-epoxy butanoates 8, respectively. Chiral intermediates such as (2R,3S)- and (2S,3R)-2-hydroxy-3-(4 -iodoindol-3 -yl)butanoate 5 for the chiral synthesis of (-)- and (+)-1 were also obtained by the enantioselective hydrolysis of the corresponding acetate 6 by lipase.